DECANE

DECANE Synonyms: AI3-24107; BRN 1696981; CCRIS 653; n-Decane; Decyl hydride; EINECS 204-6864; NSC 8781; UN 2247.

CH3 H3C

Note: According to Chevron Phillips Company’s (2005) product literature, 94.5-96.0% decane (commercial grade) contains 3-methylnonane (2.5 wt %) and 5-methylnonane (1.0 wt %). Pure grades contained 0.5 wt % isoparaffins. CASRN: 124-18-5; DOT: 2247; molecular formula: C10H22; FW: 142.28; RTECS: HD6550000 Physical state and color: Clear, colorless liquid. Reported odor threshold concentrations were 11.3 mg/m3 by Laffort and Dravnieks (1973) and 620 ppbv by Nagata and Takeuchi (1990). Melting point (°C): -30.0 (Stephenson and Malanowski, 1987) Boiling point (°C): 174.1 (Dreisbach, 1959) Density (g/cm3): 0.72991 at 20.00 °C, 0.71476 at 30.00 °C (Hahn and Svejda, 1996) 0.73357 at 15.00 °C, 0.72607 at 25.00 °C, 0.71843 at 35.00 °C (Calvo et al., 1998) 0.7262 at 25.00 °C (Aralaguppi et al., 1999) 0.72643 at 25.00 °C (Martinez et al., 2000) 0.7186 at 35.00 °C (Aminabhavi and Patil, 1997) Diffusivity in water (x 10-5 cm2/sec): 0.60 at 20 °C using method of Hayduk and Laudie (1974) Dissociation constant, pKa: >14 (Schwarzenbach et al., 1993) Flash point (°C): 46.1 (Sax and Lewis, 1987) Lower explosive limit (%): 0.8 (Sax and Lewis, 1987) Upper explosive limit (%): 5.4 (Sax and Lewis, 1987) Heat of fusion (kcal/mol): 6.864 (quoted, Riddick et al., 1986) Henry’s law constant (atm⋅m3/mol): 5.59 at 25 °C (calculated from water solubility and vapor pressure, Tolls, 2002) Interfacial tension with water (dyn/cm): 51.2 at 20 °C (Girifalco and Good, 1957)

52.26 at 20 °C (Fowkes, 1980) 53.2 at 22 °C (Goebel and Lunkenheimer, 1997) 51.30 at 25 °C (Jańczuk et al., 1993) 52.97 at 10.0 °C, 52.67 at 15.0 °C, 52.33 at 20.0 °C, 51.98 at 27.5 °C, 51.77 at 25.0 °C, 51.51 at

30.0 °C, 51.26 at 32.5 °C, 51.06 at 35.0 °C, 50.83 at 37.5 °C, 50.53 at 40.0 °C, 50.13 at 45.0 °C, 49.78 at 50.0 °C, 49.45 at 55.0 °C, 49.21 at 60.0 °C (Zeppieri et al., 2001)

Ionization potential (eV): 9.65 (Lias, 1998) Soil organic carbon/water partition coefficient, log Koc: Unavailable because experimental methods for estimation of this parameter for aliphatic hydrocarbons are lacking in the documented literature Octanol/water partition coefficient, log Kow: 6.69 (estimated using HPLC-MS, Burkhard et al., 1985a) Solubility in organics: Miscible with hexane (Corby and Elworthy, 1971) and many other hydrocarbons (e.g., hexane,

cyclohexane). In methanol, g/L: 62 at 5 °C, 68 at 10 °C, 74 at 15 °C, 81 at 20 °C, 89 at 25 °C, 98 at 30 °C, 109 at

35 °C, 120 at 40 °C (Kiser et al., 1961). Solubility in water: 2.20 x 10-5 mL/L at 25 °C (Baker, 1959) 52 µg/kg at 25 °C (McAuliffe, 1969) 19.8 µg/kg at 25 °C (Franks, 1966) 9 µg/L at 20 °C (distilled water), 0.087 mg/L at 20 °C (seawater) (quoted, Verschueren, 1983) 46 µg/L at 25 °C (shake flask-GC, Tolls et al., 2002) Vapor density: 5.82 g/L at 25 °C, 4.91 (air = 1) Vapor pressure (mmHg): 2.7 at 20 °C (quoted, Verschueren, 1983) 1.35 at 25 °C (Wilhoit and Zwolinski, 1971) 3.9 at 41.6 °C (Dejoz et al., 1996b) Environmental fate: Biological. Decane may biodegrade in two ways. The first is the formation of decyl hydroperoxide, which decomposes to 1-decanol, followed by oxidation to decanoic acid. The other pathway involves dehydrogenation to 1-decene, which may react with water giving 1-decanol (Dugan, 1972). Microorganisms can oxidize alkanes under aerobic conditions (Singer and Finnerty, 1984). The most common degradative pathway involves the oxidation of the terminal methyl group forming the corresponding alcohol (1-decanol). The alcohol may undergo a series of dehydrogenation steps, forming decanal, followed by oxidation forming decanoic acid. The fatty acid may then be metabolized by β-oxidation to form the mineralization products, carbon dioxide and water (Singer and Finnerty, 1984). Hou (1982) reported 1-decanol and 1,10-decanediol as degradation products by the microorganism Corynebacterium. Decane is readily degradable in fresh and saline waters. Biodegradation half-lives of decane in

Zoetman et al., 1980). Photolytic. A photooxidation reaction rate constant of 1.16 x 10-11 cm3/molecule⋅sec was reported for the reaction of decane with OH in the atmosphere (Atkinson, 1990). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Decane will not hydrolyze because it has no hydrolyzable functional group. Toxicity: LC50 (96-h) for Cyprinodon variegatus >500 ppm using natural seawater (Heitmuller et al., 1981). LC50 (72-h) for Cyprinodon variegatus >500 ppm (Heitmuller et al., 1981). LC50 (48-h) for Daphnia magna 18 mg/L (LeBlanc, 1980), Cyprinodon variegatus >500 ppm (Heitmuller et al., 1981). LC50 (24-h) for Daphnia magna 23 mg/L (LeBlanc, 1980), Cyprinodon variegatus >500 ppm (Heitmuller et al., 1981). LC50 (inhalation) for mice 72,300 gm/kg/2-h (quoted, RTECS, 1985). Heitmuller et al. (1981) reported a NOEC of 500 ppm. Source: Major constituent in paraffin (quoted, Verschueren, 1983). Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996). California Phase II reformulated gasoline contained decane at a concentration of 1,120 mg/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 300 and 42,600 µg/km, respectively (Schauer et al., 2002). Uses: Solvent; standardized hydrocarbon; manufacturing paraffin products; jet fuel research; paper processing industry; rubber industry; organic synthesis.